Synthesis and Activity Study of 1,2-Benzisothiazol-3-one Derivatives

doi:10.6023/cjoc202311021

Abstract

1,2-Benzisothiazol-3-one (BIT) exhibits limited antibacterial activity, prompting the search for new antibacterial drugs. In this study, BIT was used as the starting compound to synthesize 17 new N-substituted alkoxymethylbenzoisothiazolone derivatives through one-pot reaction method involving BIT, aldehyde, and alcohol. The reaction pathways were investigated using density functional theory (DFT), and the inhibitory activity of the new compounds against bacteria, fungi, and crop pathogens was evaluated. The results demonstrated that these compounds displayed strong inhibitory effects on Staphylococcus aureus and Candida albicans, with most compounds exhibiting minimum inhibitory concentrations (MIC) ranging from 1 mg/L to 4 mg/L. Compounds BIT-5, BIT-9, BIT-10, and BIT-11 exhibited high inhibitory activity against various bacteria and fungi tested, particularly against agricultural crop disease fungi such as Sclerotinia sclerotiorum, Fusarium pseudograminearum, Fusarium graminearum, and Gaeumannomyces gramims, with MIC values in the range of 5~10 mg/L, which has further research value.

Key words: 1,2-benzisothiazolin-3-one, derivative, antibacterial activity

Cite this article

Limin Wang, Xiaoyu Song, Senxiang Cheng, Tong Chen, Deyun Cui. Synthesis and Activity Study of 1,2-Benzisothiazol-3-one Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1897-1906.

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Fig. & Tab. 11

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化合物	大肠杆菌	金黄色葡萄球菌	铜绿假单胞菌	白色念珠菌	金灰青霉	黑曲霉	绿色木霉
BIT	—	—	—	—	60	>100	20
左氧氟沙星	0.5	1	8	>128	—	—	—
BIT-1a	>128	2	>128	2	100	>100	100
BIT-2	32	1	64	2	100	>100	80
BIT-2a	>128	4	>128	4	>100	>100	>100
BIT-3	64	1	128	1	80	>100	>100
BIT-3a	>128	4	>128	8	>100	>100	>100
BIT-4	64	1	64	2	>100	>100	>100
BIT-4a	>128	4	>128	16	>100	>100	>100
BIT-5	128	2	128	2	60	60	20
BIT-5a	>128	4	>128	4	>100	>100	>100
BIT-6	>128	1	>128	2	60	>100	60
BIT-7	>128	8	128	2	80	>100	60
BIT-7a	>128	4	>128	8	>100	>100	>100
BIT-8	>128	2	>128	4	100	100	>100
BIT-9	>128	1	>128	4	80	80	100
BIT-10	>128	4	>128	2	100	100	80
BIT-11	>128	2	>128	8	80	>100	100
BIT-12	>128	1	>128	4	>100	>100	>100

化合物	大肠杆菌	金黄色葡萄球菌	铜绿假单胞菌	白色念珠菌	金灰青霉	黑曲霉	绿色木霉
BIT	—	—	—	—	60	>100	20
左氧氟沙星	0.5	1	8	>128	—	—	—
BIT-1a	>128	2	>128	2	100	>100	100
BIT-2	32	1	64	2	100	>100	80
BIT-2a	>128	4	>128	4	>100	>100	>100
BIT-3	64	1	128	1	80	>100	>100
BIT-3a	>128	4	>128	8	>100	>100	>100
BIT-4	64	1	64	2	>100	>100	>100
BIT-4a	>128	4	>128	16	>100	>100	>100
BIT-5	128	2	128	2	60	60	20
BIT-5a	>128	4	>128	4	>100	>100	>100
BIT-6	>128	1	>128	2	60	>100	60
BIT-7	>128	8	128	2	80	>100	60
BIT-7a	>128	4	>128	8	>100	>100	>100
BIT-8	>128	2	>128	4	100	100	>100
BIT-9	>128	1	>128	4	80	80	100
BIT-10	>128	4	>128	2	100	100	80
BIT-11	>128	2	>128	8	80	>100	100
BIT-12	>128	1	>128	4	>100	>100	>100

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